Food or edible material: processes – compositions – and products – Products per se – or processes of preparing or treating... – Flavor per se – or containing flavor or flavor improver of...
Reexamination Certificate
2003-06-11
2004-10-19
Wong, Leslie (Department: 1761)
Food or edible material: processes, compositions, and products
Products per se, or processes of preparing or treating...
Flavor per se, or containing flavor or flavor improver of...
C426S534000, C426S590000, C426S650000
Reexamination Certificate
active
06805893
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to new 3-mercapto-alkanols enriched in particular stereoisomers, to flavoring compositions containing and to food or beverage products flavored with at least one of these enriched compounds, and to a method for the preparation of both diastereoisomers of 3-mercapto-2-methyl-butan-1-ol.
BACKGROUND OF THE INVENTION
In the food and beverage industry flavors play a critical role in the appreciation of food and beverage products. Hereafter the term flavor shall also include aroma and/or taste and in the following context all these terms are used interchangeably.
Several mercapto-alkan-1-ol compounds have been identified as flavorants in food products. Thus, 3-mercapto-hexan-1-ol has been identified in the yellow passion fruit (
Passiflora edulis
f. flavicarpa) (K. -H. Engel, R. Tressel,
J. Agric. Food Chem
. 1991, 39, 2249), in Sauvignon blanc wine (T. Tominaga, A. Furrer, R. Henry, D. Dubourdieu,
Flavour Fragrance J
. 1998, 13, 159; P. Werkhoff, M. Güntert, G. Krammer, H. Sommer, J. Kaulen,
J. Agric. Food Chem
. 1998, 46, 1076), and in red Bordeaux wine (P. Bouchilloux, P. Darriet, R. Henry, V. Lavigne-Cruège, D. Dubourdieu,
J. Agric. Food Chem
. 1998, 46, 3095), and is usually described as having passion fruit and grapefruit character.
3-mercapto-3-methyl-butan-1-ol has been found in roasted coffee (W. Holscher, O. G. Vitzthum, H. Steinhart,
J. Agric. Food Chem
. 1992, 40, 655) and in Sauvignon blanc wine (T. Tominaga, A. Furrer, R. Henry, D. Dubourdieu,
Flavour Fragrance J
. 1998, 13, 159). The flavor description by Holscher et al. is sweet, soup-like.
3-mercapto-2-methyl-propan-1-ol has been identified in red Bordeaux wine (P. Bouchilloux, P. Darriet, R. Henry, V. Lavigne-Cruége, D. Dubourdieu,
J. Agric. Food Chem
. 1998, 46, 3095) and has been described as broth, sweat-like.
The German Offenlegungsschrift 2316456 describes &ggr;-mercapto-alcohols and their formate and acetate esters as important odorants and flavorants that are useful for the preparation and modification of a broad range of flavor compositions. These compounds have been described as faint green, onion-like, sulfury and sweaty with a broad range of taste thresholds.
New 3-mercapto-alkan-1-ols for use as flavor ingredients and/or as flavor enhancers are provided.
SUMMARY OF THE INVENTION
The invention is directed to new 3-mercapto-alkanol compounds. One of these compounds is 3-mercapto-2-methyl-butan-1-ol (formula I)
and stereoisomers of 3-mercapto-2-methyl-butan-1-ol, in which the compound is either enriched for the unlike isomer relative to the like isomer, or is enriched for the like isomer relative to the unlike isomer. The compounds may be enriched for the particular isomer at various ratios.
The invention is also directed to a 3-mercapto-2-methyl-butan-1-ol flavor composition enriched in the unlike isomer relative to the like isomer at ratios of >3:1, >4:1, >6:1, >10:1, >20:1, 30>:1, or >40:1, or enriched in the like isomer relative to the unlike isomer at ratios of >10:1, >20:1, >30:1, >40:1, >50:1, or >100:1. The flavor composition may be enriched in the particular isomer. In one embodiment, the enrichment for unlike isomer relative to the like isomer is in the range of about 6:1 to about 50:1. In another embodiment, the enrichment for unlike isomer relative to the like isomer is in the range from >3:1 to about 50:1. In one embodiment, the enrichment for like isomer relative to the unlike isomer is in the range from about 30:1 to about 100:1. In another embodiment, the enrichment for like isomer relative to the unlike isomer is in the range from >10:1 to about 100:1.
The invention is also directed to a method of flavoring a product by adding to the product 3-mercapto-2-methyl-butan-1-ol (formula I) and stereoisomers of 3-mercapto-2-methyl-butan-1-ol, in which the compound is enriched in the unlike isomer relative to the like isomer, or enriched in the like isomer relative to the unlike isomer, in an amount effective to flavor the product. The product may be a food or beverage, and the compounds may be enriched in the unlike isomer relative to the like isomer at ratios of >3:1, >4:1, >6:1, >10:1, >20:1, >30:1, or >40:1, or in the range of >3:1 to about 50:1, or in the range of about 6:1 to about 50:1, or may be enriched in the like isomer relative to the unlike isomer at ratios of >10:1, >20:1, >30:1, >40:1, >50:1, or >100:1, or in the range of >10:1 to about 100:1, or in the range of about 30:1 to about 100:1.
The invention is also directed to a food or beverage product containing a flavor/aroma composition comprising a 3-mercapto-2-methyl-butan-1-ol enriched in the unlike isomer relative to the like isomer, or enriched in the like isomer relative to the unlike isomer.
Another of these compounds is 3-mercapto-3-methyl-hexan-1-ol (formula II)
and stereoisomers of 3-mercapto-3-methyl-hexan-1-ol.
In one embodiment, the compound is a stereoisomer of 3-mercapto-2-methyl-butan-1-ol having a relative unlike (u) configuration (formula III)
or the enantiomer of III.
In an alternative embodiment the compound is a diastereomer of 3-mercapto-2-methyl-butan-1-ol having a relative like (l) configuration (formula IV)
or the enantiomer of IV.
The above compounds may be used as flavorants in foods and/or beverages. The 3-mercapto-2-methyl-butan-1-ol and stereoisomer compounds provide cooked vegetable and meaty flavor/aroma notes to food products. The (S) isomer of 3-mercapto-3-methyl-hexan-1-ol enhances meaty notes, while the (R) isomer of 3-mercapto-3-methyl-hexan-1-ol enhances natural fruity character of exotic fruit flavors.
The invention is also directed to a flavor composition containing one or a combination of these compounds. In alternative embodiments, the flavor composition contains (rac)-3-mercapto-3-methyl-hexan-1-ol, (S)-3-mercapto-3-methyl-hexan-1-ol, or (R)-3-mercapto-3-methyl-hexan-1-ol. The compound in the flavor composition is at a concentration in the range of about 0.01 ppb to 50 ppm. The invention is also directed to a food or beverage product containing the above flavor compositions.
The invention is further directed to a method of flavoring a product, such as a food, beverage, oral hygiene product, pharmaceutical, or chewing gum, by adding one or a combination of the above compounds in an amount sufficient to flavor the product. The concentration of the compound may be in the range of about 0.01 ppb to 50 ppm.
The invention is still further directed to methods to synthesize 3-mercapto-2-methyl-butan-1-ol and stereoisomers, and 3-mercapto-3-methyl-hexan-1-ol and stereoisomers.
DETAILED DESCRIPTION
It has now been found that two new mercapto-alkanols, namely 3-mercapto-2-methyl-butan-1-ol of formula I
and 3-mercapto-3-methyl-hexan-1-ol of formula II
including all possible stereoisomers have very interesting flavor properties that are strongly dependent on the absolute and relative configurations of the compounds.
Especially interesting are the flavor properties of the two diastereoisomeric forms of 3-mercapto-2-methyl-butan-1-ol. As known to one skilled in the art, it will be appreciated that (u)-3-mercapto-2-methyl-butan-1-ol of formula III includes both (S)(R) and (R)(S) enantiomers (formulas IIIa and IIIb, respectively).
As known to one skilled in the art, it will also be appreciated that (l)-3-mercapto-2-methyl-butan-1-ol of formula IV includes both (R)(R) and (S)(S) enantiomers (formulas IVa and IVb, respectively).
which is depicted generally as
It has been found that the (u)-3-mercapto-2-methyl-butan-1-ol enantiomers exhibit a strong onion-like note, with a surprisingly extreme low odor threshold value of 4 pg/l air. Due to this extremely strong aroma, (u)-3-mercapto-2-methyl-butan-1-ol of formula III is a valuable flavor ingredient, and even at concentrations of down to 0.01 ppb in water, the flavor of these compounds can be recognized. It has been found that the enantiomers of formula III are useful to enhance the meaty, boiled meat c
Acuna Gonzalo
Gautschi Markus
Kumli Frank
Schmid Joachim
Zsindely Janos
Givaudan SA
Wong Leslie
Wood Herron & Evans L.L.P.
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